((2S,4S,5R)-4-Hydroxymethyl-2-methyl-5-phenyl-pyrrolidin-2-yl)-methanol | 648419-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ((2S,4S,5R)-4-Hydroxymethyl-2-methyl-5-phenyl-pyrrolidin-2-yl)-methanol
• 英文别名: [(2S,4S,5R)-2-Methyl-5-phenylpyrrolidine-2,4-diyl]dimethanol；[(2R,3S,5S)-5-(hydroxymethyl)-5-methyl-2-phenylpyrrolidin-3-yl]methanol
• CAS: 648419-86-7
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: PMQNUBUKVXLMBS-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 ((2S,4S,5R)-4-Hydroxymethyl-2-methyl-5-phenyl-pyrrolidin-2-yl)-methanol 以 吡啶 为溶剂， 反应 16.0h， 以67%的产率得到N-acetyl-r-2S,c-4R-di(acetoxymethyl)-2-methyl-c-5S-phenylpyrrolidine
  参考文献：
  名称：

  X=Y−ZH compounds as potential 1,3-dipoles. Part 43. Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl acrylate

  摘要：

  Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt(3) X-Ray crystal structures of representative cycloadducts establish that the absolute configuration of the newly established pyrrolidine stereocentres is independent of the metal salt and the size of the pyrrolidineC(2)-substituent for a series of aryl and aliphatic imines.

  DOI：

  10.1016/0040-4020(94)00940-v
• 作为产物：
  描述：

  methyl 2-(benzylideneamino)propanoate 在 lithium aluminium tetrahydride 、 silver(I) acetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 ((2S,4S,5R)-4-Hydroxymethyl-2-methyl-5-phenyl-pyrrolidin-2-yl)-methanol
  参考文献：
  名称：

  金属离子催化的α-氨基酯亚胺的不对称1,3-偶极环加成反应

  摘要：

  在银（I），锂（I）和al（I）盐的存在下，在室温下完全不对称诱导进行一系列α-氨基酯的亚胺与丙烯酸手性薄荷酯的环加成反应。2-氨基甲基吡啶的亚胺反应相似。当钛（IV）配合物用作催化剂时，会发生环加成区域化学的逆转以及完全不对称的诱导。通过X射线晶体学已经确定了环加合物之一的绝对构型。

  DOI：

  10.1016/s0040-4039(00)97119-3

文献信息

• X=Y−ZH compounds as potential 1,3-dipoles. Part 43. Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl acrylate
  作者：Darrin A. Barr、Michael J. Dorrity、Ronald Grigg、Simon Hargreaves、John F. Malone、John Montgomery、James Redpath、Paul Stevenson、Mark Thornton-Pett

  DOI：10.1016/0040-4020(94)00940-v

  日期：1995.1

  Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt(3) X-Ray crystal structures of representative cycloadducts establish that the absolute configuration of the newly established pyrrolidine stereocentres is independent of the metal salt and the size of the pyrrolidineC(2)-substituent for a series of aryl and aliphatic imines.
• Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines of α-amino esters
  作者：Darrin A Barr、Michael J Dorrity、Ronald Grigg、John F Malone、John Montgomery、Shuleewan Rajviroongit、Paul Stevenson

  DOI：10.1016/s0040-4039(00)97119-3

  日期：1990.1

  Cycloaddition of a range of imines of α-amino esters to homochiral menthyl acrylate proceeds with complete asymmetric induction at room temperature in the presence of silver(I), lithium(I) and thallium(I) salts. The imine of 2-aminomethylpyridine reacts similarly. Reversal of cycloaddition regiochemistry, together with complete asymmetric induction, occurs when titanium (IV) complexes are used as catalysts

  在银（I），锂（I）和al（I）盐的存在下，在室温下完全不对称诱导进行一系列α-氨基酯的亚胺与丙烯酸手性薄荷酯的环加成反应。2-氨基甲基吡啶的亚胺反应相似。当钛（IV）配合物用作催化剂时，会发生环加成区域化学的逆转以及完全不对称的诱导。通过X射线晶体学已经确定了环加合物之一的绝对构型。